20 Questions to Ask Early On in Dating

Last Updated: November 23, 2023

Dating Tips

When it comes to dating, you don’t want to waste time trying to figure out if the person sitting across from you is a good match. That’s why knowing what questions to ask when dating someone new can be so helpful!

Take a look at these conversation topics to figure out whether you have a spark or should try your luck with someone else.

First date questions

These questions will give you a very basic understanding of who someone is and whether you might have chemistry with them:

What is something you would write a book about if you could? Or if writing isn’t your thing, what’s something that you would direct a movie about, or dedicate a podcast to?

Instead of asking something simple like, “What are your hobbies,” this question will allow them to talk freely about something that really gets them going! One person might answer with something they’re good at, like running or painting, while others might see it as a soapbox for them to air their grievances about why their favorite show got canceled. There are no wrong answers here! After all, you can truly make a podcast about anything.

What are your thoughts on horoscopes? Overrated or totally accurate?

Let’s be honest, everyone is either super into horoscopes or couldn’t care less. And it’s probably a good idea to clear it up now.

Are you an early bird? Or a night owl? And do you think it’s possible to have a relationship with someone who is the opposite?

The first part of this question is pretty standard. But the second half is where things get interesting! Some people actually prefer to have a partner who has the opposite routine than them because it allows them to work or do solo activities while their partner sleeps. Others are firm in wanting a partner whose routine can sync up with their own.

If your best friend wrote your online profile, how would they describe you?

Sometimes it’s hard for us to hype ourselves up. But giving someone the space to talk about themselves from the perspective of their best friend can help them feel more comfortable.

If money was no option, how would you spend your time?

It may seem like a casual question, but how someone answers can tell you a lot about their hopes, dreams, and priorities. Would they use their free time setting up a charity organization? Searching for the best dumpling restaurant in the world? Would they reconnect with nature and forsake society altogether?

Questions to ask when dating someone a few weeks

Questions to ask when dating someone a few weeks.jpg

Let’s say you’ve gone on a few dates and you think there might be something worth pursuing with this person! Here are a few questions to get to know them a little better:

If you could be president for one day and could successfully implement one program, what would it be?

Nervous about getting political? Don’t worry. This question will give you a pretty good idea about where your partner stands without being confrontational.

Who is the family member you feel the closest connection to and why?

Family can be a tricky subject for a lot of people. So, it’s good to have a few positive questions to ask when dating someone new to ease into the conversation.

Have you traveled out of your hometown, your state, the country? If yes, what was the biggest lesson you took away from the experience?

Maybe they have something heartfelt to say about how humbling it is to experience a culture totally different than yours. Or, maybe they’ll say that traveling made them grateful for the comforts of home. Either way, there’s probably a pretty good story—and a hint of a worldview—in their answer.

What is your non-therapy therapy?

We can all agree that actual therapy is a green flag, right? Well, what about the other activities or practices that bring them peace and comfort? Maybe it’s a walk in the woods, writing, chatting with friends.

Is food an emotional experience for you? Or more of a necessity?

This is one of those questions that will let you know if this person will match your energy. If you’re a foodie yourself, then you’ll definitely want someone who is equally adventurous. If you’re kind of lukewarm about food, then you won’t mind someone saying they’re not excited about it either.

Questions to take you to the next level

Okay, you’re definitely starting to fall for this person, even though you’ve only been dating for a short while. Here are some questions to ask when dating someone you want to get more serious with:

Do you see yourself living here for the rest of your life? Or would you like to move someday?

We can’t predict the future, but it’s not a bad idea to talk about where in the world this partner wants to be.

The dreaded family question: Do you want kids?

Eek, we know. It’s a loaded question. But it’s best to get it on the table before you get more serious.

What are some of the characteristics of a good partner for you?

Often, it’s our own ego that prevents us from asking the one question that could make our relationships happier: what do you want? So, at this stage, don’t be afraid to ask what this person sees as important in a partner. If their list of characteristics is wildly different from who you are, it might be time to reassess. Or, if their characteristics are somewhat similar to your personality, you can use it to guide you towards being an even better partner.

Questions to ask when dating someone casually


Not everyone dates in order to find their soulmate. And you might be looking for something more casual than long-term. So what kinds of questions can you ask that will make for a more enjoyable fling?

What draws you to a casual relationship?

Everyone has a different reason for wanting something casual. Some may be too busy for a traditional relationship. Others may feel jaded with the current dating scene.

How often are you interested in meeting up?

When casually dating someone, you don’t have to worry about acting aloof or playing the call-them-after-three-days games. Instead, get specific about how often you’d like to see each other so that you can make the most of your time together.

Is there anything in particular that would make this more fun for you?

If you want a casual relationship to work, you’ll want to get to know what a potential partner likes. They may be interested in a flirty weekend trip or a few steamy messages between dates. Asking these questions early on in dating will allow you to keep the flame alive longer.

Is there anything off-limits in terms of conversation?

In traditional dating, you’ll eventually want to ask more personal questions as a way to build intimacy. But, casual dating doesn’t play by the same rulebook! So, make sure to chat early on about what level of emotional intimacy you’re both comfortable with.

What do you think we should do if one or both of us starts to develop feelings?

Even if you have experience with casual dating, it’s always good to have a plan for what to do if one or both of you falls for the other.

Best practices for asking questions early on in dating

Okay, you’re ready to start asking questions! But, keep these final tips in mind:

  • Give them the benefit of the doubt. Sometimes people say some wacky things when they're nervous. So, resist the urge to run away if you hear an answer you don’t like. Instead, take the time to clarify when they’re feeling more relaxed.
  • Allow them to plead the 5th. When you’re just starting to date someone, you might not have built enough trust for them to be an open book. Give them some time to warm up by not pressuring them to answer questions they’re not ready for.
  • Be thoughtful with your own answers. Dating is a two-way street, so you’ll also need to get vulnerable! Your ability to answer these questions will make the conversation feel more equal and relaxed.
  • Have fun! You’re not a journalist (well, at least not on your date), so loosen up a little! These are important questions to ask when dating someone new, but they should also lead to interesting and enjoyable conversations!

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